The 12 comfiest knee-high boots to build your outfits around this winter, tested by style editors

Best overall: DuoBoots Haltham

Colors: Black, light brown, and dark brown leather; light brown and black suede.

No other brand does inclusive boot sizing like DuoBoots. Not only can you pick from tall, standard, and petite heights, you can also pick from nine different shaft widths, ranging from just under 12 inches to almost 21 inches.

Different editors with different calf lengths and widths tried the Haltham, and we were all incredibly impressed with the custom-like fit. It’s a rarity that a single style works for so many different needs, but DuoBoots has gotten it right.

I tested the Haltham in a petite fit with a 13.8-inch shaft width. Since I’m 5-foot-2 (the same height as Sally, pictured above), most boots bunch around my ankles or come up over my knees. But these gave me a smooth, flattering fit. Plus, they’re incredibly comfortable to walk in.

Lauren Savoie, our former deputy executive editor, tested the Haltham in a tall fit and with an 18.5-inch shaft width, and she had a similarly glowing review: “As a tall plus-size lady, I’ve pretty much never been able to find an exact fit on knee-high boots. I can’t stress how much of a game changer the custom calf sizing is. I really feel like I’ve found a super dialed-in fit that feels extremely comfortable.”

In our DuoBoots review, she continues: “There’s even room for me to go up a calf size if I eventually want to buy a pair to wear over jeans. That’s a rarity in the plus-size world. Since getting my first set of DuoBoots over a year ago, I’ve occasionally considered other boot brands, but the lack of calf-sizing specificity from most brands (like, what does “extra wide calf” even mean?) turns me away. I’d much rather invest in a pair of custom-fit boots that I know will work for my body and, with some care, will last for years.”

Best leather: Naturalizer Axel Weatherproof Knee High Boot

Colors: Black and brown leather

This is the first of a few Naturalizer picks on this list — and for good reason. The brand, always known for going above and beyond when it comes to comfort, has stayed true to its DNA by including all the practical bells and whistles you could want.

The Axel Weatherproof Knee-High Boot has a padded footbed and a special lining in the shaft to keep warmth in. It’s also completely waterproof and designed to withstand heavy rain. But just because it is a sensible shoe doesn’t mean it has to look like a sensible shoe.

I love how elegant these boots look. The nearly three-inch block heel adds height and chicness despite the fact that they feel like sneakers. Plus, the streamlined design has a lengthening effect on your legs, made even more prominent by the boost you get from the heels. 

Best budget: Ermonn Womens Knee High Boots

Colors: Brown, black, light brown, wine, khaki

You can get these boots on Amazon for under $60. They have a slew of rave reviews, with many buyers mentioning how comfortable they are, how they look more expensive than they cost, and how they run true to size. The only note is that the shaft on the boot is a tiny bit tall, so it may come up a little over your knee if you’re under five-foot-three.

Most comfortable: Bared Footwear Remiz

Colors: Black and brown leather

“I brought these boots with me on a 10-day trip to Europe. I hadn’t broken them in whatsoever, so I also made sure to bring extra Band-Aids, assuming I’d be in for a world of hurt.

Reader, I’m so glad to report I was dead wrong. These buttery-soft leather boots pulled on effortlessly, zipped up and fit perfectly around my calves and ankles, and the cushioned footbeds meant I had sneaker-like comfort while walking 7 miles a day on slick, uneven cobblestone sidewalks. I’ve broken in a lot of leather shoes over the years, but rarely ever do I find a pair that leaves me blister-free.

Now, I know $509 is a lot for one pair of knee-high boots. But when you consider the podiatric research that goes into crafting its biomechanical footbeds, along with the quality of the smooth, stretch leather, it adds up. So if you like their sleek, fitted look and plan to walk a lot, I fully support the splurge.” — Gabrielle Chase, senior associate style editor, Insider Reviews

Best croc-embossed: Inez Paloma

“When I first saw this pair of boots, my wife had to basically pick my jaw up off the ground. I mean, they’re utterly gorgeous, to say the least. They also come in wide calf and footbed sizing, which just made me even more sure that someone designed these special for me. I get so many compliments every time I wear them — to the point that I’ve been buying outfits specifically to pair with these boots! 

“The croc-embossed finish has a luxurious sheen to it that makes the Inez Paloma boots look particularly elegant, and the texture and shine gives even the simplest sweater dress outfit a sophisticated flare. I love the brownish-burgundy pair I tested, but if you prefer a simpler look you can also opt for black leather or chestnut suede. Perhaps the biggest selling point was that I, a notorious heel hater, was able to wear these four hours on end while walking in the city thanks to the boots’ well-constructed arch support.” — Sally Kaplan, executive editor, Insider Reviews.

See our full thoughts on the Paloma and other super comfy and stylish boots from Inez in our Inez Review.

Most stylish: Naturalizer Deesha Knee-High Boot

If you’re looking for a knee-high boot that’s equal parts stylish and wearable, the Naturalizer Deesha is a great pick. The design has a little extra height in the front, which gives it a soft, rounded shape. It’s the kind of subtle detail that makes these boots look more elevated than your standard knee-highs, and the brand’s signature comfort features mean that I’ve never had any issues with these giving me blisters or making my feet hurt at the end of the day.

I went for the leopard-print suede version because it’s such a fun statement piece, but the Deesha also comes in classic neutrals if you want something more understated.

Best stretchy: Vivaia Tara Pro Water Repellent Wool Knee-High Boots

Colors: Black, brown, black and red, burgundy, navy blue

“Vivaia’s Tara Pros have been my go-to rain boots. I’ve worn them throughout the especially rainy stretch of weekends we’ve had in New York City, and falling raindrops would bead on the uppers and brush off with a simple swipe. I also tested them by pouring water over them before putting them on, and the flexible knit fabric wicks moisture so effectively that I was honestly impressed. You couldn’t wear these as waders, but they’re a more stylish alternative to rubber rain boots.” — Gabrielle Chase, senior associate style editor, Insider Reviews

Best pointed-toe: Ally Boot

If you’re always struggling with getting the perfect fit when it comes to boots, Ally is the place to go.

You can pick between three different footbed widths: medium, wide, and extra wide. Plus, you can also choose between a regular or roomy shaft width. I highly recommend taking their fit finder quiz to determine which size is best for you. And if you want to be super sure, you can even order a complimentary measurement kit that will come in the mail.

This custom-feeling fit is the best part about Ally. You can absolutely feel the difference when the toe box cradles your forefoot perfectly, and the shaft doesn’t strain or droop.

These are priced higher than many of the boots on this list, but you’re paying for comfort, a perfect fit, and high-quality materials.

Best riding boot: Naturalizer Rena 2 Riding Boot

This is the third Naturalizer pick on this list, so you know that Naturalizer boots are something special. We love the brand for its comfort and for its prices, which reflect the quality of the product.

Freelance style writer Rebecca Strong tested these for her article on the most comfortable boots and loved the style and walkability.

She writes: “Riding boots are a classic for a reason: they work with everything from floaty floral dresses to distressed boot-leg jeans. But the features that make the Naturalizer Rena 2 stand out are the eye-catching criss-cross straps, flattering almond-shaped toe, and polished buckles. The fact that they zip on and off is a plus for me, too, because pull-on styles don’t tend to be as svelte in the ankle area.”

Plus, they’re exceedingly walkable. “Most importantly, though, thanks to the 1-inch block heel, removable insole, and Contour+ Comfort technology, I definitely wasn’t racing to tear these off at the end of my work day,” she says.

Best kitten heel: Inez Mila

Colors: Black suede, espresso snake embossed, silver, black leather

We first discovered this brand when we tested a bunch of shoes for our Inez review. We were obsessed with how elegant and stylish the boots are — but perhaps even more impressed with how walkable even Inez’s highest heels are.

The Mila was one of my personal favorites. It’s endlessly versatile and I love wearing it with sheer tights, peeking out from a maxi skirt, or even paired with bootcut jeans. The silhouette is also the moment and I spotted tons of similar styles at 2024 Fashion Week. 

Best suede: Scarlett Chase Lola 75 Stretch High Boot

Colors: 12 including black, camel, red, purple, bright pink

I cannot get over how stunning these Scarlett Chase heeled boots are. Scarlett Chase is quickly becoming one of my holy grail brands for finding shoes that are just as stylish as they are comfortable. And just look how incredibly stylish these Lola 75 boots are — to match that top-tier level in comfort is a huge feat. 

The shorter version of these boots made our list of the best ankle boots for women and I can’t decide which one I like better. Both are gorgeous, statement-making, and feel so supportive that I could wear them all day.  

Best cowboy boots: Tecovas Annie

Leather colors: 10 including black, white, dark brown, beige, and light blue

Suede colors: Dark blue, light brown

When it comes to quality cowboy boots, you can’t get much better than Tecovas. The brand topped our list of the best cowboy boots for men and the best cowboy boots for women since they craft their boots with the most authentic materials and have a cult following among Western wear enthusiasts. It takes over 200 careful steps to create one of these rugged masterpieces, which is why getting these for under $300 is a great value. 

Learn more about the creation process in our full Tecovas Dean boots review.